| N^α-9-芴甲氧羰基-N^ε-叔丁氧基羰基-L-赖氨酸的合成研究 |
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| 引用本文： | 刘美艳,曾佑林,杨鹏彪,李叶华,罗冬文,苏胜培.N^α-9-芴甲氧羰基-N^ε-叔丁氧基羰基-L-赖氨酸的合成研究[J].精细化工中间体,2009,39(5):26-29. |
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| 作者姓名： | 刘美艳 曾佑林 杨鹏彪 李叶华 罗冬文 苏胜培 |
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| 作者单位： | 1. 湖南师范大学化学与化工学院,湖南,长沙,410081
2. 长沙同瑞医药科技开发有限公司,湖南,长沙,410013 |
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| 基金项目： | 湖南省教育厅资助科研资助项目 |
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| 摘 要： | Using H2O-acetone as solvent, sodium bicarbonate as acid binder and catalyst, N^ε-tert-butoxycarbony- L-lysine copper （Ⅱ） complex was synthesized successfully by Nε-tert-butoxycarbonylation of L-lysine copper （Ⅱ） complex which was furnished by protection of the α-amino and carbonyl of L-lysine with copper （Ⅱ） sulfate pentahydrate. The free α-amino was released from Nε-tert -butoxycarbonylation of L-lysine copper （Ⅱ）complex promoted by copper catching regent, and followed by Nα-9-fluorenylmethyloxycarbonylation catalysted by sodium carbonate with H2O-acetone as solvent to form Nα-9-fluorenylmethyloxycarbonyl-Nε-tert-butyloxycarbonyl-l-lysine （Fmoc-L-Lys （Boc） -OH）. The effects of four kinds of copper catching regents on the Nα -9- fluorenylmethyloxycarbonylation were studied, and the results showed the excellent copper catching regent were sodium sulfide and 8-hydroxyquinoline. The reaction conditions of Nα-9-fluorenylmethyloxycarbonylation such as ratio of Nε-tert-butoxycarbony-L-lysine copper （Ⅱ） complex to Fmoc-Osu, reaction time, reaction temperature were investigated in detail. The optimum reaction conditions were obtained as follow： the mole ratio of Nε-tert- butoxycarbony-L-lysine copper （Ⅱ） complex to Fmoc-Osu is 1.00 ： 0.98, the reaction temperatureare is room temperatureare and the reaction time is 3 h. Under those conditions, Fmoc-L-Lys （Boc）-OH was reached in 91.7% yield with 99.1% purity.
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| 关 键 词： | L-赖氨酸 L-赖氨酸铜络合物 脱铜试剂 Fmoc—L—Lys(Boc)-OH |
Study on the Synthesis of Fmoc-L-Lys(Boc)-OH |
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| LIU Mei-yan,ZENG You-lin,YANG Peng-biao,LI Yie-hua,LUO Dong-wen,SU Sheng-pei.Study on the Synthesis of Fmoc-L-Lys(Boc)-OH[J].Fine Chemical Intermediates,2009,39(5):26-29. |
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| Authors: | LIU Mei-yan ZENG You-lin YANG Peng-biao LI Yie-hua LUO Dong-wen SU Sheng-pei |
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| Affiliation: | LIU Mei-yan, ZENG You-lin, YANG Peng-biao, LI Yie-hua, LUO Dong-wen, SU Sheng-pei (1. College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, China; 2. Changsha Tongrui Pharmaceuticals Science Technic Development Co.,Ltd., Changsha 410013, China) |
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| Abstract: | Using H2O-acetone as solvent, sodium bicarbonate as acid binder and catalyst, Nε-tert-butoxycarbony-L-lysine copper (Ⅱ) complex was synthesized successfully by Nε-tert-butoxycarbonylation of L-lysine copper(Ⅱ) complex which was furnished by protection of the α-amino and carbonyl of L-lysine with copper (Ⅱ) sulfate pentahydrate. The free α-amino was released from Nε-tert-butoxycarbonylation of L -lysine copper (Ⅱ)complex promoted by copper catching regent, and followed by Nα-9-fluorenylmethyloxycarbonylation catalysted by sodium carbonate with H2O-acetone as solvent to form Nα-9-fluorenylmethyloxycarbonyl-Nε-tert-butyloxycarbonyl-l-lysine (Fmoc-L -Lys (Boc)-OH). The effects of four kinds of copper catching regents on the Nα-9-fluorenylmethyloxycarbonylation were studied, and the results showed the excellent copper catching regent were sodium sulfide and 8-hydroxyquinoline. The reaction conditions of Nα-9-fluorenylmethyloxycarbonylation such as ratio of Nε-tert-butoxycarbony-L-lysine copper (Ⅱ) complex to Fmoc-Osu, reaction time, reaction temperature were investigated in detail. The optimum reaction conditions were obtained as follow: the mole ratio of Nε-tert-butoxycarbony-L-lysine copper (Ⅱ) complex to Fmoc-Osu is 1.00∶0.98, the reaction temperatureare is room temperatureare and the reaction time is 3 h. Under those conditions, Fmoc-L-Lys (Boc)-OH was reached in 91.7% yield with 99.1% purity. |
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| Keywords: | Fmoc-L-Lys(Boc)-OH |
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